The Masterful, History-Making Portraits of Barack and Michelle Obama

Isaac Kaplan
Feb 12, 2018 8:30PM

Kehinde Wiley, Barack Obama, 2018. © 2018 Kehinde Wiley. Courtesy of the National Portrait Gallery, Washington D.C.

Amy Sherald, Michelle LaVaughn Robinson Obama, 2018. Courtesy of the National Portrait Gallery, Washington D.C.

The official portraits of former United States President Barack Obama and former First Lady Michelle Obama were unveiled at an emotional and historic ceremony at the National Portrait Gallery in Washington, D.C. on Monday morning.

The stunning depiction of President Obama, by artist Kehinde Wiley, and of his wife, by Amy Sherald, drew gasps and applause as each subject and artist together removed the black veils covering the portraits for a dramatic reveal.

Both Wiley and Sherald faced an unprecedented and monumental task: to capture the first African Americans elected to serve as president and first lady in a building built by slaves. But neither artists’ brush failed under the weight of history. The portraits are deft, thoughtful comments on race and representation in America that also provide an intimate encounter with the psyche of their individual subjects.

The results certainly pleased the sitters. Wiley’s portrait shows a seated and solemn Obama leaning forward as if in conversation, his arms crossed, against a background of dense and verdant foliage. The choice of flowers—chrysanthemums, jasmine, African blue lilies—nod to Obama’s connection with Chicago, Hawaii, and his late Kenyan father, respectively.

“How about that?” asked a smiling President Obama of the work. “That’s pretty sharp.”

Michelle Obama—who, in choosing the Baltimore-based Sherald, went with a far less-established painter than Wiley—also praised her portrait. “Let’s just start by saying ‘wow,’” she said. “Let’s just take a minute.”  

Sherald portrayed the First Lady in the artist’s characteristic grey skin tones, wearing a mostly black and white gown by the designer Michelle Smith. The dress featured modernist designs that reminded Sherald of Mondrian, but she said it was also inspired by the “quilted masterpieces” created in Gee’s Bend, a remote African American community in Alabama.

The two works will go on public view Tuesday at the National Portrait Gallery, which holds roughly 1,600 other likenesses of former presidents in its collection—though few are as expressive as those of the 44th president and the first lady.

“I am thrilled to welcome Kehinde Wiley and Amy Sherald into our collection,” said director Kim Sajet, who praised them for “taking the best of portraiture traditions and adding a fresh layer.”

© 2018 Pete Souza. Courtesy of the National Portrait Gallery, Washington D.C.


It was impossible not to feel the historic nature of the event, held on Abraham Lincoln’s birthday. Neither the President nor his wife have had a formal portrait commissioned before—high school yearbooks notwithstanding, joked Obama. For the artists chosen, it was an opportunity to have their work showcased at the highest level, as objects of international interest.

“The ability to be the first African American painter to paint the first African American president of the United States,” said Wiley, “It doesn’t get any better than that.”

Just as the Obamas were the first African American family in the White House, they are now the first African Americans in the National Portrait Gallery’s collection of presidential portraits. The National Portrait Gallery was established in 1962, and is housed in the Old Patent Office Building in Washington’s Chinatown.  

At the ceremony, the First Lady said she was thinking of “girls and girls of color who in years ahead will come to this place, and they will look up, and they will see an image of someone who looks like them hanging on the wall of this great American institution,” she said. “I know the impact that will have on their lives, because I was one of those girls.”

Her husband, too, stressed the importance of representation and how politics and power dictate who goes unseen. He praised Wiley, who often plucks his subjects off the street and places them into an art-historical context of royal portraiture, for shining a spotlight on and recognizing the grace of those who do the “stuff that makes this country work but are so often out of sight and out of mind.”

“This portrait is fabulous,” said Eugenie Tsai, senior curator at the Brooklyn Museum who organized Wiley’s 2015 retrospective there. She remarked on how the use of a floral background undercuts traditional masculine notions of power. “I think it’s one of his best,” she added of the work, likening it to Gilbert Stuart’s iconic depictions of George Washington from the 18th century.

The way in which the foliage evokes Obama’s past but also obscures parts of the president’s body was intentional, the artist said; a way to represent the fight between a president’s story and the president as a human being.

“Who gets to be the star of the show?” Wiley asked. “The story, or the man who inhabits that story?”

© 2018 Pete Souza. Courtesy of the National Portrait Gallery, Washington D.C.

Monday’s reveal followed months of excitement that began building immediately after the selection of Wiley and Sherald as portraitists was announced in October. Their bold and conceptual style marked a departure from the choices of previous presidents who have opted for more traditional artists, spurning those favored by the contemporary art mainstream. But if the selections were a departure from history, so too was the election of an African American president.

Wiley and Sherald were chosen from among 20 potential portrait artists submitted to the Obamas before leaving the White House, with the 44-year-old Sherald added to the list “at the very last minute,” Sajet told the New York Times in October.

Unlike Wiley, who has graced the limelight since museums started staging shows of his work while the artist was still in his 20s, Sherald only recently rocketed into the public spotlight. Her evocative portraits of African Americans, depicted in meticulously chosen ensembles and portrayed against colorful backdrops, first gained attention from critics after she won the Outwin Boochever Portrait Competition in 2016, beating out 2,500 other entries to become the first woman to take home the $25,000 prize.

“Interest in her work was deep before she was awarded this honor, but the global stage on which she now finds herself is warranted and welcome,” Monique Meloche, her gallerist, wrote in an email.

In many ways, Sherald’s delayed recognition is the product of circumstance. She was diagnosed with congestive heart failure at age 31, shortly after receiving her MFA at the Maryland Institute College of Art. After blacking out in a pharmacy nine years later, she underwent a transplant, spending two months in the hospital before the procedure. Sherald also waited tables until she was 38 to support her artmaking, and again broke off her career to take care of two ailing relatives.

Wiley, age 40, has taken a more steady path to fame. He began taking art classes at age 11, going on to graduate with an MFA from the Yale University School of Art in 2001 and became an artist-in-residence at the Studio Museum in Harlem. He quickly gained fame for his evocative, lush portraits, usually of African American men. These contemporary subjects are styled as figures from art history in the vein of greats such as Diego Velázquez, Édouard Manet, and Jacques-Louis David.

© 2018 Pete Souza. Courtesy of the National Portrait Gallery, Washington D.C.

In his speech, the president joked that he had insisted for Wiley not to portray him in such regal glamour—with a scepter or on a horse. “I had to explain that I’ve got enough political problems without you making me look like Napoleon! You’ve got to bring it down a touch,” he said. To which Wiley rejoined with a laugh, “How do you explain that a lot of that is just simply not true?”

Wiley’s work has earned him mountains of praise—the New York Times called him “one of the most celebrated painters of his generation” in 2015—but he’s also faced criticism surrounding the revelation that the lush background patterns of his canvases were the product of studio assistants, or even outsourced to China. The entirety of Obama’s portrait was painted by the artist himself, Sean Kelly, his dealer, confirmed.

The chance to paint America’s first black president is the realization of a long-held dream for Wiley. The artist also remarked upon a symbiotic relationship between the painter and his subject—both were born to American mothers and absent fathers from Africa.

“It’s a personal portrait for him,” said Kelly.

A tearful Wiley also thanked his mother, who “found a way to get paint and she had the ability to be able to picture something bigger than that piece of South Central [Los Angeles] we were living in.”

Capturing the likeness of a President is almost always a novel challenge for any portrait painter. Though Wiley has painted celebrities like LL Cool J and Grandmaster Flash, both he and Sherald often select complete strangers that grab their attention as subjects—the kind of everyday African Americans erased from, and ignored by, art history. It is no surprise then that representation and race are central to both artist’s practice.

“I basically paint people who I want to see exist in the world,” Sherald said in a 2016 interview. “But then I also want to creative a narrative that's extricated from a dominant historical narrative.”

Critics had warm words for the selection of the two artists. Both Obamas are known for an engagement with modern and contemporary art unprecedented for any residents of the White House, before or since. During the Obama presidency, artwork by African Americans such as Alma Thomas and Glenn Ligon graced the walls, while 19th-century portraits were replaced with conceptual modern pieces by Robert Rauschenberg and Mark Rothko.

The choice of such artwork, and of Wiley and Sherald, showcased “the Obamas’ instincts for balancing the expected and the surprising, and for being alert to painting’s pertinence to the moment,” wrote Roberta Smith in the New York Times.

The dramatic and emotional ceremony Monday echoed that moment nearly a decade ago, when a man and his wife stood on a stage in Chicago and thanked Americans for sending them to the White House. Sherald’s and Wiley’s paintings amount to an intimate conversation with a couple changed by two terms in power, perhaps more weary from their time in office, but still imbued with the ability to inspire. Even now, even after all that has happened, the portraits bring memories of hope and anticipation, at once palpable but impossibly far away.

Isaac Kaplan